#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/16/2201667.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201667
loop_
_publ_author_name
'Hökelek, Tuncer'
'Patır, Süleyman'
'Ergün, Yavuz'
'Okay, Gürol'
_publ_section_title
;
 Ethyl 9H-1,2,3,4-tetrahydrocarbazole-3-carboxylate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1255
_journal_page_last               o1257
_journal_paper_doi               10.1107/S1600536802018871
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C15 H17 N1 O2'
_chemical_formula_structural     'C15 H17 N1 O2'
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.603(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2221(10)
_cell_length_b                   7.5133(10)
_cell_length_c                   17.539(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      10
_cell_volume                     1319.5(3)
_computing_cell_refinement       'CAD-4 Express'
_computing_data_collection       'CAD-4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2686
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1736
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0459P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                653
_reflns_number_total             2686
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6121.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C15 H17 N1 O2'
_cod_database_code               2201667
_cod_database_fobs_code          2201667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.0775(3) 0.6499(3) 0.17629(14) 0.1011(11) Uani d . 1 . . O
O2 0.2895(4) 0.6089(3) 0.23494(18) 0.0929(11) Uani d . 1 . . O
N9 -0.0190(4) 0.7672(4) 0.5127(2) 0.0670(11) Uani d . 1 . . N
C1 0.1837(4) 0.7710(4) 0.44976(19) 0.0691(12) Uani d . 1 . . C
C2 0.2005(4) 0.7823(4) 0.36529(18) 0.0754(12) Uani d . 1 . . C
C3 0.1295(4) 0.6329(4) 0.31537(19) 0.0705(13) Uani d . 1 . . C
C4 -0.0198(4) 0.6330(5) 0.3125(2) 0.0777(14) Uani d . 1 . . C
C4A -0.0497(4) 0.6740(4) 0.3896(2) 0.0624(13) Uani d . 1 . . C
C5 -0.3015(5) 0.6110(5) 0.3785(3) 0.0861(15) Uani d . 1 . . C
C5A -0.1733(4) 0.6632(4) 0.4144(2) 0.0642(12) Uani d . 1 . . C
C6 -0.4034(5) 0.6221(6) 0.4186(3) 0.1003(18) Uani d . 1 . . C
C7 -0.3807(5) 0.6852(5) 0.4953(4) 0.1016(16) Uani d . 1 . . C
C8 -0.2541(6) 0.7371(5) 0.5327(2) 0.0830(14) Uani d . 1 . . C
C8A -0.1523(5) 0.7238(4) 0.4918(3) 0.0674(13) Uani d . 1 . . C
C9A 0.0416(4) 0.7363(4) 0.4505(2) 0.0572(12) Uani d . 1 . . C
C10 0.1605(5) 0.6309(5) 0.2352(2) 0.0744(15) Uani d . 1 . . C
C11 0.3266(5) 0.6034(5) 0.1596(2) 0.0920(16) Uani d . 1 . . C
C12 0.4729(4) 0.5831(6) 0.1724(3) 0.1178(19) Uani d . 1 . . C
H1A 0.2387 0.6758 0.4764 0.083 Uiso calc R 1 . . H
H1B 0.2115 0.8818 0.4765 0.083 Uiso calc R 1 . . H
H2A 0.1658 0.8955 0.3435 0.091 Uiso calc R 1 . . H
H2B 0.2949 0.7782 0.3641 0.091 Uiso calc R 1 . . H
H3 0.1642 0.5212 0.3405 0.085 Uiso calc R 1 . . H
H4A -0.0621 0.7209 0.2750 0.093 Uiso calc R 1 . . H
H4B -0.0563 0.5173 0.2954 0.093 Uiso calc R 1 . . H
H5 -0.3179 0.5688 0.3276 0.103 Uiso calc R 1 . . H
H6 -0.4890 0.5871 0.3945 0.120 Uiso calc R 1 . . H
H7 -0.4514 0.6922 0.5213 0.122 Uiso calc R 1 . . H
H8 -0.2382 0.7794 0.5836 0.100 Uiso calc R 1 . . H
H9 0.014(4) 0.805(4) 0.5572(19) 0.097(16) Uiso d . 1 . . H
H11A 0.2993 0.7123 0.1311 0.110 Uiso calc R 1 . . H
H11B 0.2830 0.5040 0.1294 0.110 Uiso calc R 1 . . H
H12A 0.5000 0.5791 0.1231 0.177 Uiso calc R 1 . . H
H12B 0.4989 0.4747 0.2003 0.177 Uiso calc R 1 . . H
H12C 0.5151 0.6822 0.2021 0.177 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C4A C9A N9 109.6(4) ?
C4A C9A C1 125.3(4) yes
N9 C9A C1 125.1(4) yes
C10 O2 C11 116.7(4) ?
C8A N9 C9A 109.2(4) ?
C8A N9 H9 122(3) ?
C9A N9 H9 129(3) ?
O1 C10 O2 122.6(5) ?
O1 C10 C3 123.7(5) ?
O2 C10 C3 113.6(4) ?
C9A C1 C2 108.7(3) yes
C9A C1 H1A 109.9 ?
C2 C1 H1A 109.9 ?
C9A C1 H1B 109.9 ?
C2 C1 H1B 109.9 ?
H1A C1 H1B 108.3 ?
C10 C3 C4 111.7(4) ?
C10 C3 C2 112.4(3) ?
C4 C3 C2 112.4(3) yes
C10 C3 H3 106.6 ?
C4 C3 H3 106.6 ?
C2 C3 H3 106.6 ?
N9 C8A C8 130.8(4) yes
N9 C8A C5A 106.5(4) ?
C8 C8A C5A 122.7(4) yes
C9A C4A C5A 107.0(4) yes
C9A C4A C4 123.9(5) yes
C5A C4A C4 129.1(4) yes
C4A C4 C3 111.2(4) yes
C4A C4 H4A 109.4 ?
C3 C4 H4A 109.4 ?
C4A C4 H4B 109.4 ?
C3 C4 H4B 109.4 ?
H4A C4 H4B 108.0 ?
C3 C2 C1 112.6(3) yes
C3 C2 H2A 109.1 ?
C1 C2 H2A 109.1 ?
C3 C2 H2B 109.1 ?
C1 C2 H2B 109.1 ?
H2A C2 H2B 107.8 ?
C5 C5A C8A 118.4(5) yes
C5 C5A C4A 133.8(4) yes
C8A C5A C4A 107.8(4) yes
C6 C5 C5A 119.6(4) ?
C6 C5 H5 120.2 ?
C5A C5 H5 120.2 ?
O2 C11 C12 107.9(4) ?
O2 C11 H11A 110.1 ?
C12 C11 H11A 110.1 ?
O2 C11 H11B 110.1 ?
C12 C11 H11B 110.1 ?
H11A C11 H11B 108.4 ?
C8 C7 C6 120.6(5) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C5 C6 C7 121.1(5) ?
C5 C6 H6 119.4 ?
C7 C6 H6 119.4 ?
C8A C8 C7 117.6(4) ?
C8A C8 H8 121.2 ?
C7 C8 H8 121.2 ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C9A C4A . 1.352(4) yes
C9A N9 . 1.378(4) yes
C9A C1 . 1.478(4) yes
O2 C10 . 1.329(4) yes
O2 C11 . 1.448(4) yes
N9 C8A . 1.377(5) yes
N9 H9 . 0.84(3) ?
C10 O1 . 1.206(4) yes
C10 C3 . 1.503(5) yes
C1 C2 . 1.528(4) yes
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C3 C4 . 1.516(5) yes
C3 C2 . 1.516(4) yes
C3 H3 . 0.9800 ?
C8A C8 . 1.381(5) yes
C8A C5A . 1.407(5) yes
C4A C5A . 1.419(5) yes
C4A C4 . 1.477(4) yes
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C5A C5 . 1.391(5) yes
C5 C6 . 1.372(5) yes
C5 H5 . 0.9300 ?
C11 C12 . 1.475(5) yes
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C7 C8 . 1.384(5) yes
C7 C6 . 1.400(5) yes
C7 H7 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 H8 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C4A C9A N9 C8A 0.2(3) ?
C1 C9A N9 C8A 178.5(3) ?
C11 O2 C10 O1 -1.8(5) ?
C11 O2 C10 C3 179.2(3) ?
C4A C9A C1 C2 17.6(4) yes
N9 C9A C1 C2 -160.4(3) ?
O1 C10 C3 C4 8.8(5) yes
O2 C10 C3 C4 -172.3(3) yes
O1 C10 C3 C2 -118.6(4) yes
O2 C10 C3 C2 60.4(4) yes
C9A N9 C8A C8 -177.6(3) ?
C9A N9 C8A C5A 0.4(3) ?
N9 C9A C4A C5A -0.6(4) ?
C1 C9A C4A C5A -178.9(3) ?
N9 C9A C4A C4 177.7(3) ?
C1 C9A C4A C4 -0.6(5) yes
C9A C4A C4 C3 11.7(4) yes
C5A C4A C4 C3 -170.3(3) ?
C10 C3 C4 C4A -167.7(3) ?
C2 C3 C4 C4A -40.3(4) yes
C10 C3 C2 C1 -172.7(3) ?
C4 C3 C2 C1 60.3(4) yes
C9A C1 C2 C3 -46.1(4) yes
N9 C8A C5A C5 -179.7(3) ?
C8 C8A C5A C5 -1.5(5) ?
N9 C8A C5A C4A -0.7(3) ?
C8 C8A C5A C4A 177.4(3) ?
C9A C4A C5A C5 179.5(4) ?
C4 C4A C5A C5 1.3(6) ?
C9A C4A C5A C8A 0.8(4) ?
C4 C4A C5A C8A -177.4(3) ?
C8A C5A C5 C6 0.9(5) ?
C4A C5A C5 C6 -177.6(4) ?
C10 O2 C11 C12 178.5(3) ?
C5A C5 C6 C7 0.0(6) ?
C8 C7 C6 C5 -0.4(6) ?
N9 C8A C8 C7 178.8(3) ?
C5A C8A C8 C7 1.1(5) ?
C6 C7 C8 C8A -0.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 248663
